Is This the Secret to Mess-Free Period Sex?

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There is nothing I love more than a bonkers analogy — especially when it involves sex — so I was pretty pleased with my semantic skills a few years back when I once whispered to a friend I had been publicly, drunkenly making out with at a bar: “We can’t hook up tonight, the game is rained out.”

“What? What game?” he replied. In his defense, it was raining outside.

“You know … the game.” I tried briefly to elaborate on my chosen imagery (“My vagina is a baseball diamond …?”) before giving up and telling him I was on my period.

Jason didn’t skip a single beat. “So? I’ve had girlfriends before. It’s not a big deal. Be an adult.” I ultimately was an adult (after much coaxing), but not without a lot of panicked giggling.

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Since Jason, a few years have passed and I have grown up considerably. I’ve become real comfortable with my vagina, and with talking about it ad nauseam. I swapped out oral birth control for a NuvaRing. I traded tampons for a menstrual cup on a bet and have loved the DivaCup for the last year, and not just because of the whimsical purple brooch that comes in the packaging (letting you proclaim to the world that you are indeed a “DIVA”), though that does help a lot. I’ve even become one of those annoying IUD evangelists, because they really are great, aren’t they? At this point, my vaginal canal is a funhouse — you really never know just what you might find in there.

But period sex? That’s one thing I hadn’t come around on. Much of this was because of the curse of semi-perpetual singledom: On one hand, casual sex romps with guys I enjoyed sleeping with could often be so sporadic, I knew I should take it where I could get it, a little period blood be damned. On the other hand, period sex is one of those ick-factor level 100 things that’s already so awkward to talk about, the idea of never having to have sex again is often more palatable than both of you being able to see the postcoital carnage on his inner thighs left behind as a macabre souvenir. I ended up defaulting to the other hand a lot.

Upon hearing that I loved the DivaCup so much, a friend suggested I try out the Softcup — a menstrual cup similar to the Diva, save for one important difference: You can have sex with a Softcup inside you. It’s purported to be mess-free, allowing the user to have her cake and eat it, too. Or, in this case, have it be eaten, I suppose.

Problem one: finding a willing participant. While I wasn’t as single this time — I had just started dating someone casually — our situation was casual enough that I felt weird making him my accomplice in period journalism.

So I went with the adult route: a fake drunk text.

“Hey, what r u up to? Me? Omg soooo wasted haha, by the way, i said id try out this thing, it’s superrrr weird but like u can have period sex with it in and there’s no mess, here look at this link. Lol.” In retrospect, despite my studiously random capitalizations, these texts would have seemed more plausibly drunken had I not sent them at 3 p.m. on a Tuesday — but Aaron, ever understanding, was game. My period, not so much. It showed up a week and a half later than normal, likely as terrified as I was.

Once it arrived, I embarked on one giggly trip to the drugstore near my office and emerged victorious with a box of Softcups. Fancying myself a DivaCup pro, I planned to put one in midday and let it carry me through coitus later that evening, just as God and the Softcup manufacturers over at Evofem, Inc. had intended. It hadn’t even occurred to me that the process of using one might be different from the DivaCup, which relies on a complicated insertion process involving a 360-degree internal twist, various levels of suction, and a lot of prayer. Luckily, the wonderful sociopaths over at WikiHow provided this tutorial, which includes an animated video on Softcup insertion and over 12 steps involving a lot of inexplicable cup tilting, and, terrifyingly, the phrase “hook it behind your cervix.” It’s now unsurprising to me that the bottom of the tutorial called for physics experts to contribute to other WikiHow articles. I suddenly regretted not taking anything past chemistry in high school.

I decided to just wait until Aaron and I were about to have sex before inserting the damn thing. (Aaron, a far more willing participant in this whole farce than I, lamented the fact that without a semi-full Softcup in, he wouldn’t get to see if our modified period sex “felt squishy.” I am perfectly fine living my life without this knowledge.) The hooking procedure wasn’t nearly as horrid as it sounded, and off we went, to our carefully pre-planned sexual encounter.

Honestly? It wasn’t so bad. Like the DivaCup, the Softcup is partially made of silicone, which conforms to your body as it heats up. Despite being significantly smaller than the Diva, the Softcup was oddly less comfortable — though between all that tilting and hooking, it stands to reason that I fucked it up. Other than that, however, it functioned as advertised: We definitely had some mess-free period sex.

To be fair, I was so paranoid about menstrual carnal relations (I have white sheets!), I was far more cognizant of realllllly wiping the last time I went to the bathroom before inserting the Softcup, which may have played a part in its being far cleaner than either of us expected. But in the name of journalism (and the name of journalism, alone), we left it in throughout the night and went for a few more rounds, just to see if it held up. I eventually got out of my head and forgot it was in there, which made the entire situation far more pleasurable. Aaron was finally able to report back, “It’s not so much that it’s squishy, it’s just that when I hit the little plastic bag, I feel like Nemo’s dad when he’s swimming through all the jellyfish with Dory in Finding Nemo.”

In the morning, I pulled out the Softcup, and one look was enough to ensure that I would never be using a Softcup again. While DivaCups retain their shape and are made for about a year of use, the disposable Softcup looked like what would be left behind if a pit bull chewed through a plastic bag. Did it do what it advertised? Absolutely. Was the period sex fun and not messy? For sure. Is my lack of willingness to partake again simply a sign of my emotional immaturity and not a fault of the product itself? You bet.

While I would happily recommend a Softcup to a friend who was looking for a way to make period sex a little neater, I don’t see myself using it again — despite the entirely pleasant and civilized evening I spent wearing one. Aaron and I only ended up lasting a few months past our Softcup experiment, and while I don’t blame period sex, I had no hesitation giving away the remainder of the package to a friend far more comfortable with her body than I.

I suspect that my misgivings about period sex stem from my general feelings about singledom. Finding someone to hook up with when single, and maintaining a façade of casualness while admitting to yourself that it’s not at all casual for you — the type of girl whose heart lives in her vagina alongside all the other things she’s shoved up there — is already a hard enough balancing act without in the addition of period sex. And while I’d like to think that being in a relationship would help me grow the pair of balls I so desperately need to be okay with ovarian function, single me just assumes that wifed-up me will be having so much regular sex (the only benefit I can see to being in a relationship, currently), that four days on the bench will be nothing but a drop in the menstrual-blood-filled bucket.